WO2009064335A1 - Séparation d'un mélange de polyols - Google Patents
Séparation d'un mélange de polyols Download PDFInfo
- Publication number
- WO2009064335A1 WO2009064335A1 PCT/US2008/011214 US2008011214W WO2009064335A1 WO 2009064335 A1 WO2009064335 A1 WO 2009064335A1 US 2008011214 W US2008011214 W US 2008011214W WO 2009064335 A1 WO2009064335 A1 WO 2009064335A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- butanediol
- mixture
- matrix
- zone
- propylene glycol
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 105
- 150000005846 sugar alcohols Polymers 0.000 title claims abstract description 71
- 238000000926 separation method Methods 0.000 title description 35
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 401
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 146
- 238000000034 method Methods 0.000 claims abstract description 93
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims abstract description 65
- 239000011159 matrix material Substances 0.000 claims abstract description 57
- -1 butanediol compound Chemical class 0.000 claims abstract description 50
- 239000012504 chromatography matrix Substances 0.000 claims abstract description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 41
- 239000000284 extract Substances 0.000 claims description 41
- 239000000463 material Substances 0.000 claims description 32
- 238000001179 sorption measurement Methods 0.000 claims description 32
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 31
- 239000011347 resin Substances 0.000 claims description 29
- 229920005989 resin Polymers 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 238000004587 chromatography analysis Methods 0.000 claims description 23
- 229940083957 1,2-butanediol Drugs 0.000 claims description 20
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 20
- 238000003795 desorption Methods 0.000 claims description 20
- 230000008929 regeneration Effects 0.000 claims description 20
- 238000011069 regeneration method Methods 0.000 claims description 20
- 230000000274 adsorptive effect Effects 0.000 claims description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000004927 clay Substances 0.000 claims description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 239000005909 Kieselgur Substances 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 239000006229 carbon black Substances 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 26
- 239000000356 contaminant Substances 0.000 abstract description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 111
- 239000000047 product Substances 0.000 description 99
- 229960004063 propylene glycol Drugs 0.000 description 71
- 235000013772 propylene glycol Nutrition 0.000 description 71
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- 230000008569 process Effects 0.000 description 34
- 229940093476 ethylene glycol Drugs 0.000 description 32
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- 238000012360 testing method Methods 0.000 description 17
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- 238000007327 hydrogenolysis reaction Methods 0.000 description 16
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- 229920005862 polyol Polymers 0.000 description 16
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- 150000003077 polyols Chemical class 0.000 description 15
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- 239000000126 substance Substances 0.000 description 13
- 239000002808 molecular sieve Substances 0.000 description 12
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 11
- 238000010828 elution Methods 0.000 description 11
- 238000002474 experimental method Methods 0.000 description 11
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 10
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- 239000003795 chemical substances by application Substances 0.000 description 10
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- 238000004821 distillation Methods 0.000 description 9
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- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 8
- 230000000155 isotopic effect Effects 0.000 description 8
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- 241000196324 Embryophyta Species 0.000 description 6
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- 239000000243 solution Substances 0.000 description 6
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 239000000440 bentonite Substances 0.000 description 5
- 229910000278 bentonite Inorganic materials 0.000 description 5
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 5
- 235000019437 butane-1,3-diol Nutrition 0.000 description 5
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
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- 150000007524 organic acids Chemical class 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 150000003138 primary alcohols Chemical class 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 239000011800 void material Substances 0.000 description 4
- AXPZIVKEZRHGAS-UHFFFAOYSA-N 3-benzyl-5-[(2-nitrophenoxy)methyl]oxolan-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1OCC1OC(=O)C(CC=2C=CC=CC=2)C1 AXPZIVKEZRHGAS-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
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- 230000008901 benefit Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
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- 238000005304 joining Methods 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
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- 244000309464 bull Species 0.000 description 1
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- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
- YMBNBZFZTXCWDV-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2,3-triol Chemical compound OCCO.OCC(O)CO YMBNBZFZTXCWDV-UHFFFAOYSA-N 0.000 description 1
- HQPMKSGTIOYHJT-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CC(O)CO HQPMKSGTIOYHJT-UHFFFAOYSA-N 0.000 description 1
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- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
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- 239000003863 metallic catalyst Substances 0.000 description 1
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- 229940078552 o-xylene Drugs 0.000 description 1
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- 238000010672 photosynthesis Methods 0.000 description 1
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- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
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- 239000010970 precious metal Substances 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
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- 239000000700 radioactive tracer Substances 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
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- 238000004088 simulation Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
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- 238000001228 spectrum Methods 0.000 description 1
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- 239000000057 synthetic resin Substances 0.000 description 1
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- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La présente invention porte sur des procédés de séparation d'au moins un composé butanediol à partir d'un mélange contenant des polyols et des composés butanediols. Le mélange de polyols contient typiquement du propylèneglycol et de l'éthylèneglycol en plus des contaminants butanediols. Les contaminants butanediols sont retirés par mise en contact du mélange avec une matrice chromatographique. Soit les composés butanediols soit les composés non-butanediols s'adsorbent sur la matrice chromatographique. Si on le désire, les composés adsorbés peuvent être élués de la matrice, purifiés et utilisés dans des produits.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98682707P | 2007-11-09 | 2007-11-09 | |
| US60/986,827 | 2007-11-09 | ||
| US12/235,192 US8177980B2 (en) | 2007-11-09 | 2008-09-22 | Separation of a mixture of polyhydric alcohols |
| US12/235,192 | 2008-09-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2009064335A1 true WO2009064335A1 (fr) | 2009-05-22 |
Family
ID=40622717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2008/011214 WO2009064335A1 (fr) | 2007-11-09 | 2008-09-26 | Séparation d'un mélange de polyols |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US8177980B2 (fr) |
| WO (1) | WO2009064335A1 (fr) |
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| CN105985220A (zh) * | 2014-11-26 | 2016-10-05 | 义守大学 | 醇类化合物的纯化方法 |
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| CN102372598A (zh) * | 2010-08-23 | 2012-03-14 | 中国石油化工股份有限公司 | 乙二醇和丁二醇的分离方法 |
| CN102372599B (zh) * | 2010-08-23 | 2013-12-04 | 中国石油化工股份有限公司 | 分离乙二醇和丁二醇的方法 |
| CN103402955B (zh) | 2011-03-14 | 2016-02-10 | 阿彻丹尼尔斯米德兰德公司 | 用于产生生物衍生的丙二醇的改进的方法 |
| JP6275278B2 (ja) * | 2014-04-10 | 2018-02-07 | アーチャー−ダニエルズ−ミッドランド カンパニー | 酸触媒の組合せ混合物を用いた糖アルコールの脱水 |
| US10017439B2 (en) * | 2014-04-10 | 2018-07-10 | Archer Daniels Midland Company | Process for the isolation of reaction products from sugar alcohol or anhydrosugar alcohol hydrogenolysis reaction mixtures using simulated moving bed chromatography |
| RU2691407C2 (ru) | 2014-04-22 | 2019-06-13 | Арчер Дэниелс Мидлэнд Компани | Усовершенствованный способ изготовления биопроизводного пропиленгликоля |
| WO2016001136A1 (fr) | 2014-06-30 | 2016-01-07 | Haldor Topsøe A/S | Procédé pour la préparation d'éthylène glycol à partir de sucres |
| EP3160928B1 (fr) | 2014-06-30 | 2023-10-25 | Topsoe A/S | Procédé pour la préparation d'éthylène glycol à partir de sucres |
| US11040903B2 (en) * | 2015-10-05 | 2021-06-22 | The Chemours Company Fc, Llc | Purification of NaCl brine containing iodine |
| WO2017095687A1 (fr) * | 2015-12-01 | 2017-06-08 | Dow Global Technologies Llc | Séparation chromatographique d'acides organiques au moyen d'un adsorbant macroporeux polymère |
| US9796948B2 (en) | 2016-01-13 | 2017-10-24 | The Procter & Gamble Company | Laundry detergent compositions comprising renewable components |
| CN108341741A (zh) * | 2017-01-23 | 2018-07-31 | 中国石油化工股份有限公司 | 一种合成气制备乙二醇的提纯精制工艺及装置 |
| CN107583308B (zh) * | 2017-10-19 | 2023-10-10 | 苏州苏震生物工程有限公司 | 一种用于1,3-丙二醇和2,3-丁二醇纯化的设备及工艺 |
| CN110665256B (zh) * | 2019-10-08 | 2021-01-08 | 中国科学院过程工程研究所 | 一种模拟移动床装置及分离多组分二元醇的方法 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105985220A (zh) * | 2014-11-26 | 2016-10-05 | 义守大学 | 醇类化合物的纯化方法 |
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| US8177980B2 (en) | 2012-05-15 |
| US20090120878A1 (en) | 2009-05-14 |
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